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Merck

A1784

Aminopterin

synthetic (organic), ≥97% (TLC), dihydrofolate reductase inhibitor, powder

Synonym(s):

(S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid

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About This Item

Empirical Formula (Hill Notation):
C19H20N8O5
CAS Number:
54-62-6
Molecular Weight:
440.41
MDL number:
MFCD00036692
UNSPSC Code:
12352200
PubChem Substance ID:
24278186
NACRES:
NA.77
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045

Key Documents

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Product Name

Aminopterin, powder

SMILES string

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

InChI

1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1

InChI key

TVZGACDUOSZQKY-LBPRGKRZSA-N

biological source

synthetic (organic)

form

powder

Quality Level

200

Gene Information

human ... FPGS(2356)
mouse ... Fpgs(14287)

description

Purity (≥98%)

color

light yellow to yellow-brown

solubility

2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)

ε (extinction coefficient)

24,500 at 282 nm in 0.1 M NaOH at 1 M, 25,700 at 261 nm in 0.1 M NaOH at 1 M, 8,100 at 373 nm in 0.1 M NaOH at 1 M

storage temp.

−20°C

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Biochem/physiol Actions

Folic acid antagonist that binds to dihydrofolate reductase and inhibits its activity.
Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

More potent, but more toxic, than methotrexate.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000490219
0000490219
0000490215
0000490215
0000473802

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Min Zhang et al.
Cell, 181(3), 637-652 (2020-04-10)
Many cytosolic proteins lacking a signal peptide, called leaderless cargoes, are secreted through unconventional secretion. Vesicle trafficking is a major pathway involved. It is unclear how leaderless cargoes enter into the vesicle. Here, we find a translocation pathway regulating vesicle
Aleem Gangjee et al.
Journal of medicinal chemistry, 48(16), 5329-5336 (2005-08-05)
We report, for the first time, the biological activities of four-carbon-atom bridged classical antifolates on dihydrofolate reductase (DHFR), thymidylate synthase (TS), and folylpolyglutamate synthetase (FPGS) as well as antitumor activity. Extension of the bridge homologation studies of classical two-carbon bridged
M Del Campo et al.
Teratology, 60(1), 10-12 (1999-07-21)
Maternal exposures to aminopterin and methotrexate have been associated with a pattern of malformation which includes prenatal-onset growth deficiency, severe lack of ossification of the calvarium, hypoplastic supraorbital ridges, small, low-set ears, micrognathia, and limb abnormalities. We report on a
Yingjuan J Lu et al.
Cell reports. Medicine, 2(10), 100422-100422 (2021-11-11)
Provoked by sterile/nonsterile insults, prolonged monocyte mobilization and uncontrolled monocyte/macrophage activation can pose imminent or impending harm to the affected organs. Curiously, folate receptor beta (FRβ), with subnanomolar affinity for the vitamin folic acid (FA), is upregulated during immune activation
Hatem A Azim et al.
Current opinion in oncology, 24(3), 325-331 (2012-02-22)
To discuss the clinical development of new formulations of old cytotoxic agents and highlight the value of adopting this strategy. Several drugs are currently in clinical development with high potential in improving clinical outcomes compared with their older counterparts. We
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